How to Be Successful with Sarah Cooper

Episode description

How do you decide when to take a huge leap in your career? What happens when your therapist thinks leaving your cushy tech job is a terrible idea—but you do it anyway? Googler-turned-comedian Sarah Cooper joins us to talk about writing satire, redefining success, and making men mad along the way.

We love Sarah because she’s funny as hell, and also incredibly open about what it’s like to trade a career in tech for the sometimes lonely—but also wildly satisfying—world of comedy.

> I have so many outlets to discover myself and who I really am, which is something that I think is just really important for a life, you know? To know you left everything on the table and you told every story that you wanted to tell and you let everyone know who you are—and you didn’t leave this world without telling everybody that.
>
> —Sarah Cooper, comedian and author of How to Be Successful Without Hurting Men’s Feelings

She tells us about:

Leaving a career at Google to perform standup and write satire all day

What happens when people think your satire is serious

How being a Jamaican immigrant taught her to observe people so she could fit in

The pros and cons of being a “people-pleaser”—and how to let go of that when it stops serving you

How keeping a “best self journal” helps her stay focused while working alone

Also in this episode

Sara and Katel talk about the big career choices they’ve made, and how they’ve built structures and support systems to make those careers work for them. Deets:

Sara celebrates seven whole years without a traditional “jobby-job,” and thinks back on Cindy Gallop’s advice that working for yourself is the least risky thing you can do

Katel tells us why she took a pay cut to run A Book Apart—and how she handles the lonely parts of working, well, alone

We both definitely wear fancy blazers at all times
> I remember being so excited to work with a much smaller team and fewer people… I was like, “oh my gosh, this is going to be so great, it’s going to be just a few people, it’s going to be really nimble.” And then I realized that most of the time it was really just going to be me working kind of by myself. And it was a lot harder than I expected because there was essentially no structure unless I made it, and it took me at least a good year to kind of figure out how I was going to work, how I was going to be productive, whether I even liked that way of working enough to keep doing it.
>
> — Katel on trading corporate life for running an indie publishing company

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Transcript

Sara Wachter-Boettcher [Ad spot] Thanks for Harvest to being our sponsor today—and for making awesome project management and time tracking tools that I rely on to keep my business running. I think you’ll love them too. They offer all kinds of reports that help you shine a light on the health of your projects, and they make it easy to track invoices and payments. Try it free at getharvest.com, and when you sign up for a paid account, you can use the code “noyougo” to save 50% off your first month. That’s getharvest.com, offer code “noyougo.” [intro music plays for 12 seconds]

SWB Hey everyone, I’m Sara!

Katel LeDû And I’m Katel.

SWB And you’re listening to No, You Go, the show about building satisfying careers and businesses—

KL —getting free of toxic bullshit—

SWB —and living your best feminist life at work.

KL “How to Be Successful Without Hurting Men’s Feelings” is the title of our new favorite book, and it’s out today. It’s written by our guest, Sarah Cooper, and we are so pumped to talk with her today. Okay, along with some extremely funny, satirical advice for getting by in the workforce, Sarah gets real about why she wrote the book, and what happens when people don’t understand that it’s satire. And how she managed a massive change in her own work life, going from being a manager at Google to a full-time comedian and writer.

SWB Yes, I was super interested in that, and I was hoping we could talk more about that transition piece. Because companies like Google are so designed to really keep you there in a lot of ways, right? You don’t just get fed at work, you also get dry cleaning and haircuts.

KL So weird.

SWB It’s super weird. [KL laughs] But they’re very—you know—once you’re in them, they can be very cushy places to be—

KL Yeah.

SWB —and they also oftentimes will feel like you’re doing exciting work, and you’re paid really well, and so there’s a lot of stuff that kind of keeps people there. I have a friend who recently mentioned that—you know—she’s been at Google a long time and the idea of leaving is really hard for her. So, it’s interesting to hear Sarah talk about leaving somewhere like Google to do something that was so uncertain and so risky, right? Like a career in comedy and writing? That’s such a dramatic pivot.

KL Yeah, I know. It is—it’s so fascinating and I loved listening to her story. But, Sara, you’ve been working for yourself for as long as I’ve known you, but that wasn’t always the case. That hasn’t been your whole career, you made a big moving from working at a traditional—you know—jobby-job to go out on your own in 2011, right?

SWB Yeah, actually October has been my seven-year working-for-myself anniversary!

KL Congrats!

[2:27]

SWB Thank you. It has been pretty great for me. I think that it’s definitely something that has suited me. But—you know—what’s really different about it compared to somebody like Sarah is that I don’t feel like I’ve taken such massive shifts. I feel like my changes have been a little more bit by bit over time. I wasn’t in a big, fancy, fully catered office with free haircuts and massages; [KL laughs] I was working at an agency with 40 people, which means I was working a lot with clients. And so my shift from working with clients at an agency to working for myself with clients was smaller. And the kind of work was similar. But I do think that over the past seven years, I’ve made more and more of those little incremental shifts, or kind of mini-pivots or whatever you want to call them, where I do feel like at this point my work has evolved so much—both in the kinds of clients I work with, the complexity of the projects, I definitely charge more [KL laughs]—lots of—lots of good stuff.

KL [laughing] Yep!

SWB But also just the makeup of my days. My day is not mostly clients, it’s—maybe that’s a third of my time. And a lot of my time is spent on things like speaking at events, writing books, doing workshops and more facilitation versus sitting down and doing the work for clients. And—you know—also running this podcast, which does take a bunch of time. And maybe someday we’ll make a bunch of money. And so I feel like on the one hand, I have quote-unquote the same business I had seven years ago, and then on the other hand, on a day-to-day basis it looks really different. And my goals have changed too. That’s one of the things I think is really interesting talking to somebody like Sarah is hearing a really different perspective on leaving a traditional kind of job and moving into something else.

KL Yeah, completely. And I mean to me, and I think a lot of people, the idea of going solo and leaving the perceived—you know—quote unquote safety of a traditional job, has seemed kind of scary. I mean, when you initially did that, what did that sort of first leap look like? Did you do anything specific to prepare—you know—financially, [laughs] emotionally, mentally?

SWB Yeah, so—you know—I think about something Cindy Gallop said to us in her interview a couple of episodes ago where she said that in—in a lot of ways, relying on another company to take care of you is the riskiest thing you can do, and that relying on yourself, in some ways, is less risky. And I think that that was something I kind of had come to on my own back then, because I felt like the company I was at—you know—didn’t value me for the reasons that I wanted to be valued. I mean I think that they did try to value me because I was doing a lot for them and they did recognize that, but it wasn’t in the way that I wanted and it wasn’t for the kind of work I wanted necessarily. And so I felt like looking out for myself was in some ways going to be better for me. What I did, though, to prepare for leaving, I did—you know—I had some savings, which was great. At the time, one of the things that was really helpful was that my expenses were very low. My husband was in graduate school, which means that he made almost no money. He was a teaching assistant while he was in graduate school, so he had a very small stipend. So it wasn’t as if I could rely on his income, but what it did mean is that we had chosen to rent a little mini-house behind a house in a neighborhood that was affordable near the university. And so we had a low rent and we didn’t have a lot of financial commitments—we didn’t have kids, we didn’t have new cars with payments or anything like that, because we had been kind of set up to live a lifestyle that made sense for a graduate student, even though I had a real job with a substantial income. So, that made it so that the—it wasn’t that I had this huge—you know—amount of financial cushion, but it did mean that the amount of money I needed to not get evicted and to keep the lights on wasn’t that high. So, one of the things that I did was I set some goals around finances. I really wanted to—I wanted to meet or exceed the income I had been making at the agency, not just because I wanted to have the same amount of money, but also because I wanted to feel like it was a way of proving to myself and maybe to the world that what I wanted to do was a real and legitimate thing that was worth paying for, and that I didn’t have to do it on somebody else’s terms. But I also thought about, “what is the minimum amount of money that I need on a monthly basis to not have life fall apart?” And when I realized that it just wasn’t that much, I thought, you know, I can scrape that together. If things are lean here and there, I can scrape that together. And that gave me a lot of confidence, so that was helpful. The other thing that I did is I knew that the company I was leaving really relied on me and so—they were going through a time of flux also, so I knew that they could really use my help for longer. So, what I did was I proposed to them that I would contract with them for a couple of months—I think three months or so I contracted with them—and so that gave me some time to kind of wean off of having that salary. And it gave them some time to get over me leaving and to have a—you know—different plan in place. And during that time I had that consistent money coming in from them, I did more of that reaching out to people in my network. And I knew people who worked at different agencies or different companies who I had maybe worked with in the past, and so they knew that it was helpful to work with somebody like me. And none of their companies had content strategy teams at the time, and so they would often bring me in and I was like the first content strategist they’d worked with on a project [laughing]. All of them now have whole content strategy departments, so I feel like they’ve kind of gotten the memo—and I don’t want to take sole credit for that by any means, that’s something that’s sort of shifted in a lot of people’s industries in general. But I think what that was really helpful, too, was that I looked at, “who do I know who is out there working in other companies I’d like to work with who has experience and can speak to the fact that if you have somebody with this skillset working on a project, you can do much better work, you can get things done much more effectively?”

[8:12]

KL Yeah. That’s so smart that you did that. And just when you think about leaving something and trying something new, it’s—you know—I think you are focused on, what does that actual moment look like when I stop doing the old thing and start doing the new thing? And the smart thing is to actually do a lot of prep work before that and kind of take stock of where you’re working, who you’re working with, and figure out where those avenues can lead to, where they can develop into something for your new project and, I don’t know, I think that… you know, that’s really helpful to hear.

SWB Yeah, I mean I don’t know that I was that planned about it, [laughs & KL laughs] but I definitely did try to do that. And I also—I’m trying to be, you know, pretty honest about some of the financial pieces of it. Because I talk to people who are often, you know, wanting to take a risk like this and the risks for them might look totally different. And I never want to, you know, lie about that, or make it seem like that’s not a big financial risk. I didn’t—like I said—I didn’t have this big cushion, but I did have relatively low risk at the time, and that’s not going to be true if somebody has, let’s say, small kids at home, or already has a mortgage, and all of your calculations have to look different. And I think that one of the things that I hear a lot of is this sort of idea that, “just jump in, do what you love, take the leap!” without talking about how often people who do that successfully had like—I don’t know—family money or a spouse with a high, stable income or whatever, right? All of these other things that made that possible for them. And so I just think it’s a disservice to not be honest about those things.

KL Yeah, it totally is. And I’ve talked about this before—I took a pay cut when I left National Geographic to come to A Book Apart, and I wouldn’t have been able to do that if I hadn’t already been established in my career, if I hadn’t already—you know—moved up the management ladder and was making a certain salary that had allowed me to save. I was also partnered with someone who had a full-time job and who we had a little bit of a buffer, so I could do that and make a change.

SWB So, what was it about that opportunity at A Book Apart that made you want it so badly you were willing to take a pay cut for it? Because working at a small company, it is riskier—you know—you said you got paid substantially less, there are not fancy offices, there are no free haircuts at A Book Apart.

[10:38]

KL [laughing] No, not yet.

SWB What made that feel worth it for you?

KL I mean, I knew it was going to be a huge opportunity and—you know—I was looking for a new challenge and that it certainly was. I knew I was going to be able to work with a whole new community of people and, you know, people doing work that I really admired and that I really wanted to be involved in. And I knew I’d be able to grow in a way that I hadn’t really been able to grow before. I was going to be able to grow my skill set, which was exciting, but also scary.

SWB What do you mean? What were some of the things that you feel like you saw in that role that you were like “ooh yeah, I want to be able to do that”?

KL I saw a chance to be a part of building something that was more or less kind of in its—you know—beginning phases. And that was super exciting. But there was also an opening to basically develop the role as I grew into it, and I’d never experienced that before. You know, I think I’d always gone into a job being like, “here is the list of responsibilities and this is more or less it.” It’s cut and dry. And this was an opportunity that I hadn’t had before where I was making it what it was, which was super cool.

SWB So, was that ever hard though? Because I think one of the big shifts there you’re describing is going from a pretty structured environment to a really unstructured environment without, you know, having like, “here’s the boundaries of what your job is and here’s, you know, who is on your team.” And you don’t have a set of colleagues that work full-time with you, it’s like people juggling multiple kind of side gigs, and A Book Apart is often one of their side gigs. Was that hard?

KL Yeah! I remember being so excited to work with a much smaller team and fewer people, because I think I was so used to working with such large teams and so many people that it felt like it was hard to really move things forward. So all of a sudden I was like, “oh my gosh, this is going to be so great, it’s going to be—you know—just a few people, it’s going to be really nimble.” And then I realized that most of the time it was really just going to be me [SWB laughs] working kind of by myself. And it was a lot harder than I expected because there was essentially no structure unless I made it, and it took me at least a good year to kind of figure out how I was going to work, how I was going to be productive, whether I even liked that way of working enough to keep doing it. And I think now it would be really hard for me to go back to a traditional office environment at least. I mean, I have a friend who has been freelancing for almost five years and they’re just realizing that it does not work for them. They need—they are realizing that they need to go to a place and do the work and then leave that place. And I very much understand that.

[13:23]

SWB Totally, yeah. I can relate to that feeling, but I’ve never quite sunk into it. I guess I’ve had moments where I feel like that, and then I’m like, “no, okay, I need to add some structure, I need to shift how I, you know, how I do things.” You know like people who talk about how they need to get dressed for the day or whatever before they start work? I’m not one of those people, but there are things that—you know—that I think about. I don’t do client work at nights or on the weekends. I do end up doing work at night or on the weekends, if I’m going to be honest with you. People sometimes ask me, “how do you do all the things that you do?” And I’m like, “I like to work and I don’t mind doing it in the odd hours.” But I don’t do client work then. I work on the podcast maybe.

KL Right.

SWB But to me, setting some of those boundaries like not doing client work and not replying to client emails late—that’s important and that’s something where I feel like it keeps it on my terms.

KL Yeah, totally. It’s like you sort of—you have to have a little bit of a sense of office hours for there to be some kind of structure. Even if it’s only in your head and—because people, a lot of people don’t know that you aren’t—in a quote, unquote office every day doing that work.

SWB I’m in a very fancy office at all times. [KL laughs]

KL You are.

SWB And I am definitely dressed up in a very fancy business outfit and I’m wearing a blazer.

KL At all times.

SWB At all times.

KL Yeah.

SWB Literally always. [KL laughs]

KL I mean, I think about that idea of sort of working from wherever and at first again, how that idea was so exciting, but how it can become such a slippery slope. For example, on one hand I was able to plan and host that bachelorette weekend that we talked about a little while back because I could handle all the logistics leading up to it—you know—in and around my daily schedule. But when the weekend came, I also worked a little during that weekend because I could and I had a lot I need and want to get done. And to your point, it’s sort of like I love a lot of the work that I do and that’s—that’s okay, that’s part of my life, but I do need to remember that I want to set some boundaries. So, it’s great to have a lot of flexibility and freedom, as long as you kind of keep an eye on where the lines are.

[15:30]

SWB Yeah! And I let myself redraw the lines. They don’t have to be consistent all the time. But to always be thinking about “okay, I am redrawing this line right now and doing a lot of work stuff during a different—a weird time, but that might not be forever, I don’t want that being normal.” I like it though. You know, I get to do things like add a few days of vacation time when I’m taking a business trip, right? So, I go to the West Coast to go to a conference and I tack on a few days and I go see my nieces in Oregon. That’s awesome, I love being able to do that and I just have to juggle other things around it, right? I don’t have to take PTO, I don’t have to budget for it that way, I just have to juggle everything else around. I also love that I can do things like schedule appointments or run errands at like 2pm on a Tuesday and that again, I just have to be able to juggle everything else around it, which is why sometimes—you know—I do stuff in the evening that I would otherwise get done during the work day, but it means that I was able to do stuff during the work day that otherwise would be a nightmare like going to IKEA on a weekend!

KL [laughing] Yes!

SWB You know? And I feel like those are good tradeoffs for me, but I always want to take stock of what those things are.

KL Yeah. Something Sarah mentioned was that work can be lonely. Were you lonely at first when you started this—you know—this endeavor, what you’re doing now? Or do you get lonely now ever?

SWB So, I don’t tend to get lonely most of the time. Sometimes in small moments, but never in a bigger way. And I think one of the reasons for that is that I know that I’m pretty social and early on, I connected with a lot of people who were doing some of the same stuff that I did. So I remember in 2011 when I first left my job, a friend started a really small little Google group for people who were doing freelance or consultancy type work in content strategy. And it was only five or six people—eight people, I can’t remember. But that was really helpful at the beginning where I felt like “oh okay, I can chat with people who are sort of facing some of the same stuff as me or I can ask questions—what do your contracts even look like? What am I doing? What’s going on?” Very basic questions. [laughs] And that group kind of petered out—sometimes those kinds of groups peter out, but it was valuable to me in the moment. And then in 2013, I helped plan a little retreat with fifteen or twenty people running small consultancies and we came out of that and started a Slack group a little while later—I think actually a year later we turned it into a Slack group—and that’s still going and that’s—it’s a place I can bounce ideas off of, ask questions. And it’s also people I just really trust, which has been helpful. The other thing that I think has really prevented me from being lonely is that I do partner with people on projects a lot and I partner with you on a ton of stuff now, Katel. So, one thing that I’ve noticed is that I don’t work on A Book Apart and you don’t work on my client projects or come with me when I speak at conferences usually, but I feel like I have kind of a work partner where you kind of know what’s going on with my work and I know what’s going on with your work and we have enough work we’re doing together that—I don’t know—it feels like a colleague!

[18:29]

KL Ahhh, I love that so much! I agree, I feel the same way and it’s been such a cool thing to have developed where it’s like all of a sudden if we want to have a co-working day, we could do that.

SWB Totally! Plus we get to talk to so many fucking awesome people together, which is something that I really, really love. So, why don’t we do that?

KL [Ad spot] So, before we talk to Sarah, we’ve got to talk about something actually pretty related to her work—reading, writing, and creativity. Our friends at Harvest told us those things are super important to them, especially when it comes to making sure more diverse voices have a chance to share their ideas. So, Harvest has pledged to spend 4% of its profits each year to causes that help more people from all backgrounds read, write, and get creative. Two groups they support that you might want to check out are 826 National, which supports seven writing and tutoring centers for youth across the country, helping them write with confidence and originality. Check them out at 826national.org. And Graywolf Press, a nonprofit literary publisher that champions books from underrepresented voices. They’re at graywolfpress.org.

SWB I love this so much because I think about all the incredible writers we’ve had on the show so far. Like Sarah, of course, you’re going to hear from her in just a second, or Keah Brown from last week, or Nichole Chung a few weeks ago. And then, of course, Carmen Maria Machado back in the spring—you know—her book was actually published by Graywolf Press! And I think about how—you know—the world just needs more writers like them and organizations like 826 and Graywolf are really crucial to making that happen. So I love that we’re able to spotlight them and—you know—writing and creativity are so important for everyone. So, even if you’re not going to be a capital-W writer, Harvest has noted that as a remote company with people in a lot of different time zones, they rely on written words to get things done and collaborate and that reading and writing skills make it possible for them to do that and make them successful. So, they want to support more people in gaining them and so do we. So thanks, Harvest, for caring about literacy and creativity and check out 826 National and Graywolf Press for more. [music fades in, plays for five seconds, and fades out]

Interview: Sarah Cooper

SWB Sarah Cooper is a comedian, writer, and self-proclaimed trash-talker based in New York City. She runs thecooperreview.com, a wildly popular satirical blog about business culture, and her first book, 100 Tricks to Appear Smart in Meetings, was a bestseller. Now she has a new book. It’s called How to Be Successful Without Hurting Men’s Feelings and I am laugh-crying already. Sarah, welcome to No, You Go.
[21:02]

Sarah Cooper Thank you so much.

SWB So, Sarah, we were reading your new book—Katel and I were actually just talking about it—and we really were laugh-crying. In chapter one, already I was losing it. I was reading the section where you—you started having all these illustrations of hairstyles to avoid and let me just describe this for readers who haven’t been able to read the book yet. It’s this illustration series where it’s like okay—long, flowing hair is too sexy and then there’s the hair that’s up in a bun is too boring, there’s the hair that’s too old, and then the last two are where I just lost it. It’s the one that’s like “too black”—natural hair, right? And then “way too black,” which is braids. Okay, so the book is full of illustrations like this and activities and basically advice for women to be successful, but don’t be too successful. How did you get to this place where you decided to write a satirical book of “non-threatening leadership strategies for women”?

SC Well, it started as a blog post called “9 Non-Threatening Leadership Strategies for Women” and I wrote it two years ago—and it was sort of based on my experience kind of making myself more passive and trying to be more pleasing in the office and sort of getting called out on being a little too aggressive with my opinions and seeing other women get called out on the same things. And so this idea of being threatening when, in fact, we’re actually just being direct or straightforward or saying the same thing that a man would say made me think it would—it’s kind of like the perfect thing for satire where you’re trying to tell women “this is how you be less threatening,” but really the way you were going to act in the first place was already not threatening. So, that led to that first comic, which I almost didn’t publish because I have a group of friends and family that I sort of run things by before I publish anything. And I did get the feedback that this might be construed as offensive and people might take it too seriously and I might see [laughs]—I might be seen as someone who is anti-woman for giving this advice. And so, I really worked on it to try and make it as obvious as possible that it was a joke, so the advice sort of gets more silly towards the end of the post where the very last thing is “wear a mustache so that people will think you are a man and that way you won’t even have to be less threatening.” After that, I published it and it just sort of went viral in the same way that “10 Tricks to Appear Smart in Meetings” went viral and really hit a nerve and people still did think that I was serious and didn’t realize that I was not actually telling people to put on a fake mustache. But I think a lot of people just sort of saw themselves in a lot of the advice. And so that was kind of the initial spark of the idea for this book and I started writing a different book actually, last year—and I wasn’t going to write this book, especially after the election. I thought that there was just a sense of hopelessness that all women sort of felt and I didn’t know if there was a way to create something that would be funny, but also kind of not dismissive of how women were feeling. And so it—it did take me a little while to figure out how I could do it and I think what happened was I started to get angry and I think—you know—women started to go from sad to pissed and I think when I became pissed I was like, “you know what? This ridiculous. We have all of these rules everyone is trying to tell us to follow, they’re contradictory and we actually can’t win because no matter what we do, it’s not good enough and it’s not right.” And I think that that was especially how I felt with Hillary Clinton’s campaign. It was like she didn’t smile too much or she smiled too much or she was “too prepared,” I think was something that someone said, which just made me so livid. I was like, “wait a second. [laughs] If you’re too prepared, that’s not good enough?” So, it just got me so frustrated and so that’s when I was like, “you know what? I can make fun of this and I can kind of do it in a way that’s funny, but also kind of speak to how frustrating a lot of these rules are and this situation is and a lot of how women are feeling in the workplace in terms of how we should present ourselves when really we just want to be ourselves without being judged for all of these little things.

[25:28]

SWB Yes. I mean, there is so much kind of what I would say is shitty advice for women at work that is basically giving them these pointers for how to like “hey, here are some tips to suppress how you really feel all the time and act more like a man,” right? That’s kind of what they boil down to—

SC Yeah.

SWB —and so it’s interesting that you had that much of a problem of people not realizing what you were doing was satire. It seems very obvious to me.

SC [laughs] Well, I think some women were like, “you know what? I’’—they are actually on my side without realizing that they’re on my side. I think that’s the funniest part because they’ll be like, “you shouldn’t be telling women to do this, women should just act the way that they want to act and if men are offended, then screw them.” And I’m like, “yeah, exactly, that’s the point of what I’m trying to say, [KL & SWB laugh] thank you for pointing that out.” So it’s more people not—you know—it’s more people that are kind of on my side that just kind of don’t realize that I’m not actually telling people to act like this, I’m saying that we shouldn’t be telling people to act like this and that’s kind of a running thread throughout a lot of the stuff that I do—it’s bad advice. Don’t take my advice, do the opposite of the thing that I’m telling you to do and that’s a—a lot of what this is as well. But yeah, people still take it seriously and I’ve got to laugh sometimes at that.

SWB So, I’m curious—you’ve touched on this a little bit. Do you ever find yourself feeling frustrated or getting into some awkward space where you’re trying to write comedy about actual awful things that happen to real women all the time? Does that ever sort of get you down? Or does it feel like a positive outlet for you? I guess at some level it must since you [laughing] are writing a lot of comedy about it!

SC [laughs] You know what? When you take something seriously and it feels kind of sacred, you are like “I don’t want to make fun of that because I really feel strongly about that” and so it did feel like a bit of a stretch and that’s why I wasn’t going to write it at first. And then especially with the harassment chapter—that chapter almost didn’t make it in there just because I—but it had to because then I was so angry about all of these things that women have to deal with. This idea that if we get harassed by someone who is a high performer and is a really incredible contributor to the company, that somehow makes it so that they can’t do anything about it because they need that person. [laughs] It’s just this idea that companies—a lot of companies—don’t seem to care about how they’re getting to their goals, they just care that they get to their goals and so they—there’s a lot of people who kind of get trampled on in that process. And so I think that what ends up happening is I’m a little scared to make fun of something or it’s a little bit too raw to make fun of it, but then the sort of frustration makes it so that I can’t help but make fun of it because I really, really need to point this out and I really—this is just something that I really want to say about it.

[28:14]

SWB So, I know that a lot of your work sort of stemmed from your experience in kind of a past life working at Google for a number of years, kind of working in the tech industry. You’ve said that it has given you plenty of material, and I’m wondering if we can go back to that a bit. Can you tell us a little bit about sort of both how you got started in comedy and in tech and how the two kind of intertwined?

SC Yeah, it’s kind of a messy story. I always wanted to do something with performance and theatre and acting, and I kind of did it on and off while I was working. And I found stand-up because I wanted to be a better actress, and I kind of wanted to be more myself on stage and on camera. And so I decided to just get on stage at an open mic. And I drank a lot and got very drunk and got up on stage and told this story about dating and it was—it was very nerve-racking. But then I got up there and I felt very comfortable and I realized that I really liked writing for myself and I really liked being myself more than pretending to be—a character? That’s kind of—that was something that I was doing sort of in between working for Yahoo and Google and then I continued to do stand-up while I was working at Google and I would get my coworkers to come to my shows and I started to write a little bit more about what it was like to work with them and sort of making fun of the software engineers there and they—you know—loved that. They’re some of the funniest people I’ve ever met. I didn’t really realize that there was this sort of opening for satire in the corporate world before I wrote “10 Tricks to Appear Smart in Meetings,” which is really based on observation from sitting in meetings and—while I was supposed to be paying attention and contributing, I was making observations about what my coworkers were doing and especially the things that people were doing to make it seem like they knew what they were talking about when really most people weren’t paying attention at all. And I just always found it fascinating that certain people were seen as the smart ones. To me, almost everything is a sort of performance. And it’s also… I’m an immigrant. I was born in Jamaica. And so I think I’ve always kind of been like, “well, what’s the thing that I can do in this situation to make it look like I can fit in here and I’m part of it?” And so I was always sort of watching. And so I think a lot of it was just I really like observing all of those things and the first time I put that together was in “10 Tricks to Appear Smart in Meetings” and it really just resonated with people and that’s kind of what started my writing career that—as it is right now because that took off so much that I ended up leaving Google and—and writing my first book about it.

[31:02]

SWB Yeah, I think from that original post my favorite tip was maybe number six, which was “ask ‘will this scale?’ no matter what.” [KL laughs]

SC Yeah.

SWB Because, obviously, that’s the kind of thing I’ve heard a lot and it’s the kind of thing that is just said when you don’t know what else to say. And I think that that’s something that you really pinpointed so well is the way that people will sort of come up with these so called smart, insightful questions that are really just stock questions that they use to sound like they know what they’re talking about.

SC Yeah.

SWB Something that I want to touch on though—that you mentioned a minute ago that I think is really interesting, is you mentioned sort of being an immigrant and moving to this country from Jamaica and feeling like that gave you more of a sense of observing what other people are doing and figuring out what is the norm here. Sounds like maybe from a young age you became really attuned to needing to code switch and sort of trained yourself to always be identifying what the code is that’s happening, so you can flip on your “okay, I’m working at Google now” script and kind of blend. Is that something you feel like is a strong piece of your experience?

SC That’s funny, I’ve never thought of it as code switching, I’ve always thought of it as people pleasing. [laughs] I’ve always been a huge just people pleaser, which is part of myself that I absolutely hate and I did it with—you know—sort of my parents, I did it with my friends, and I did it at work. I did it in relationships. And it took me a long time to realize that a lot of times I was doing and saying things that I didn’t actually think or feel just because I thought that’s what was wanted or needed by other people in that situation. So yeah, I mean I think that I developed that from a very young age. I have [laughs]—I have this memory of being very young, and I couldn’t read yet, and I was sitting at a breakfast table with my dad and he was reading the paper and he got to the comics section and he slides me the comics section and he says, “read this, it’s funny, you’ll laugh.” And he didn’t realize that I couldn’t read yet. And so I didn’t want to say, “Dad, I can’t read” [laughs] so [KL & SWB laugh] I looked at the comics and I just started laughing—I just started pretending to enjoy myself so that my dad would think that I was doing what he wanted me to do. And I feel like that was my earliest memory of just being like, “oh, they think that I should do this, so I’ll do this”—you know? But it took a long time for me to step outside myself and realize I don’t have to do that. I can say and do what I feel.

[33:31]

SWB And so I’m curious—as you were sort of starting your career working in tech and sort of going in with that people pleaser mentality, what was that experience like for you?

SC Very successful, I have to say. I joined Google and was within a few years promoted to manage the team. And I did very well there, people loved working with me, [laughs] people loved having me in their meetings. You know, I think people pleasing is—it will get you to middle management. I don’t know if it will get you to be like a VP, but definitely as a woman especially, if you’re a people pleaser, I think that it can get you pretty far. The only thing is, you’re going to get something that you might not want, which is what I had. [laughs] You know, I became a manager and I was in a lot of meetings and I think that’s when I started to realize that I wasn’t being as creative as I wanted to be, so I guess it was kind of a blessing in disguise that I came to a point where I was more passionate about writing and stand-up and all the things I was doing outside of work than I was about the things I was doing at work. But I just find it fascinating how—you know—there’s so much imitation going on in the corporate world. I mean, that’s what people are doing in terms of how they figure out “well, this is how I need to get ahead, I need to—obviously this VP is talking so passionately about this product and all these features, and so I need to talk passionately about all these products and all these features.” Now, that VP might actually be feeling those things, but then the middle manager is just sort of imitating that passion. And so, I think that that to me was a lot of the things that I was doing as well. And it’s just kind of a strange situation, because they’re like, “oh, you have to be authentic—you know—you have to be really yourself,” but then a lot of it is just a performance in a lot of ways.

SWB You mentioned how much of a people pleaser you always were, but it seems like almost flipping when you started writing the satirical posts because they’re fundamentally making waves. And I’m wondering if that was ever sort of a scary decision for you to make.

SC It was. I mean, even as innocuous as “10 Tricks to Appear Smart in Meetings” was, I was so scared to post it because I didn’t want my coworkers to think I was making fun of them, because I was making fun of them. And I didn’t know if they would read it and I would ruin some relationships. So, that was really scary, but then a crazy thing happened. It came out, everybody read it, everybody loved it, they all started asking me if they could be featured in my next posts and they do this thing in a meeting and maybe that’s another trick I could put in there. And so that was kind of the first stepping stone of like “oh, this is okay!” And I will say that comedy for me definitely is sort of a defense mechanism. I can kind of hide behind the satire of it a little bit in order to say what I really feel. I feel like this is part of my growth is to say it in a satirical funny way, and then kind of get up the courage to say what I really feel and what I really think and be really committed to that. But it is really scary to put myself out there even a little bit, and even setting up a newsletter and sending out emails, and even when I had just forty people, I felt terrified to just send out my newsletter. It was just—it took a long time, but it’s been really great. You know, I think it’s been exactly what I needed in order to become more of who I am instead of this person that I think everyone wants me to be.

[37:08]

SWB I’m curious too, you talked about your newsletter. We mentioned at the top of the show The Cooper Review, which is the satirical blog that you run and I’m curious how and when did that get started and how did that build its audience?

SC So, I posted “10 Tricks to Appear Smart in Meetings” on Medium at first because I didn’t have a blog. And then when it got—it was starting to get millions of views, I was like, “wait a second, I should be getting some of that traffic,” so I created thecooperreview.com about—I want to say—a month or so, or maybe six to eight weeks after that blog post came out. And then I started using the post on Medium to sort of drive people to my website and get people to sign up for my newsletter and started to grow my audience that way.

SWB And so you also mentioned a lot about feeling a lot of fear about posting it and then getting a lot of positive feedback, but did you also get negative feedback? Have you received much criticism or, you know, trolls or kind of angry folks?

SC Not from my coworkers, but from—yeah, random strangers. People get very angry, especially on LinkedIn [laughs] when you think that you’re trying to tell people how to—how to look smart in meetings because they take their meetings very seriously. So, I get people saying, “well, you shouldn’t—you shouldn’t try to look smart, you should just be smart” and I’m like “okay, thank you.” [SWB laughs] Yeah, so that’s kind of funny, but then I also get—you know—I wrote a post about gaslighting, which also made it to the book as well, and I got a woman who wrote to me and said that her boss did this to her and it was very painful and—and how she usually finds my things very funny, but this was just very painful for her and she didn’t appreciate it. She didn’t think it was great for me to write this. And I was very sensitive to that, so I wrote her back and said “you know, part of the reason that I write this stuff is because I want people to be more aware of it and I think that—you know—like G.I. Joe says, “knowing is half the battle.” And so when you are aware that these things are happening, then you can do something about it, then you can say, “hey, this is what’s happening. I’m not crazy, you’re making me feel like I’m crazy.” And she wrote back and it was really nice. She was like, “yeah, that is true, that is a good point. If I had known that that was what was happening at the time, that might have helped me.” So, I have situations like that, I have, I’ve gotten some hate mail about this book. It’s not even out yet, no one can read it yet, but just the title is making people upset. A man wrote and said he would definitely not be buying my book [laughs] because it was offensive to men. It’s really, really funny actually. The subject of the email is “blatant sexism.” It says, “I won’t be buying your How to Be Successful Without Hurting Men’s Feelings. If I wrote a book called ‘How to Be Successful Without Hurting Women’s Feelings,’ no publisher would touch it and I would be lambasted for writing it in the first place, even when calling it satire. What appalls me the most is not that you wrote it, but that most men will ignore the blatant sexism, uncomfortably laugh it off, and pretend it doesn’t hurt because that is somehow more manly. I’m man enough to call you out on it, Sarah Cooper. [laughs and KL and SWB laugh loudly with her]

[40:13]

SWB Is it too late to get that as a back cover blurb? [all laugh]

SC I know, I know. It was so perfect because I just love that—I love that “oh, most men are just going to laugh it off and just—and hide their pain” and I’m like, “welcome to our world. This is what we do all the time.” So, when I first got that, I was like, “oh my god, this is—I’m offending people, I’m offending people” and then the second I sort of shared it with a few friends, they were like, “oh my gosh, this is hysterical, you have to share this with everybody.”

SWB It is quite funny and it’s also it’s like oh my gosh, you couldn’t even have the title of your book about not hurting men’s feelings out [

KL laughs] without hurting this man’s feelings.

SC Exactly, exactly.

SWB He’s so sensitive! You know, sometimes I just think men are too sensitive.

SWB Exactly, exactly. When I read your work, I feel like it comes from a perspective that I relate to a lot and obviously all of the content about—you know—being harassed at work or being looked over for promotions, all that kind of stuff, I’m like, “okay, this really resonates for somebody who’s a woman.” But I know that you have male readers and I’m curious if you get a different kind of feedback from men who read your work?

SC I think there’s just a range. I mean, I think there’s men who—god bless them—they feel like men and women should be equal and so we shouldn’t treat them differently. And it’s really hard for them to just accept the fact that yeah, we would like to be treated differently, but we haven’t been. And that’s the point. The other thing that frustrates me is that—and this happens with men and women too—it’s just like, “well, why didn’t you write a book about this?” Like this guy. “Why didn’t you write a book about women’s feelings?” It’s like there’s a specific audience and there’s a specific thing I’m trying to say and I’m sorry I couldn’t write a book for everybody, but that’s not how books work, I can’t do that. And so I think that there’s men in that camp—I think there’s men in the camp of “oh this is going to be great for my—my wife, or my girlfriend, or—you know—a friend of mine who is in the working world” and they probably don’t think that—that it will help them that much and I think that that’s fine, too. Maybe some of it will sort of—I appreciate that and I obviously it will be great that they want to share it with their female friends, but I think that the men who actually say, “I want to read this, I want to know what this perspective is like”—those are the men that just—they make me so happy. I always think about after the election; my husband is a straight white man and I was really upset after the election and he said to me, “you know, Sarah, I understand this is different for you.” And that’s all he had to say. You know, all he had to say was just appreciate the fact that this is different for me than it is for him and that’s all I want men to do is just say, “hey, this is an experience.” This is an experience that we have and these are things that we have to deal with that you don’t have to deal with and yes, we appreciate that there are things you deal with that we don’t have to, but can we just talk about us just one second? So, I think those are the men that I’m hoping to get to more of and I definitely see that. I have a great—a good deal of men who really support me and really support my work and are not even remotely offended by this title and actually see how they can learn something from it too.

[43:25]

KL Yeah. It’s so funny hearing you say all of this and then at the end of the day, it’s still—just to underscore it—we’re really not—it’s not a lot that [laughing] men would have to do. It’s like just paying attention—

SC Right.

KL —and being a little more self aware and—you know—leaving that channel open. Thinking a little bit more about your career and your work as a comedian and an author, was it scary to leave the perks and stability of a giant company like Google? Is there anything that you miss from that?

SC It was terrifying and it took me a long time [laughs nervously] and no—everybody was pretty sure that I was making a mistake. Even my therapist was like, “you know, you should stay there at Google.” [laughs] My family, my fiancé at the time—now husband. Because the thing is, I met my husband at work and he’d see me at work and I was happy, you know? I really liked those people and I really enjoyed being there, and Google is such a comfortable place to be. Everything you could possibly want is there. I probably took advantage of the nap pods too many times, [KL & SWB laugh] but it was great—it was great. And so the thing that I tell you I would miss the most is having a place to go and be comfortable and being around people that I just really respect and admire and make me laugh. I miss that very much because I didn’t realize how lonely writing was going to be, I didn’t realize how much I would enjoy sometimes being alone, but then really, really, really need to talk to people and—so now it just takes an extra effort that I didn’t have to do before, to talk to people and go outside and go do things and in order to get that stimulation and find that new material and all of that stuff. So, it took me a while and I was panicking for at least the first six months after I left, but I realized that it was a bigger risk not to leave than it was to stay because I could always go back. And once I told my boss I was leaving and he said I could always come back if I wanted to, that made me feel like, “okay, I can do this.”

KL That’s great. I’m glad that you had that and I completely get that apprehension about making such a big change—you know—not just like this is a big career change, but this is a big change in how I operate on a day to day basis. That’s huge. So—you know—today, these days, what does a typical week look like?

[45:57]

SC Well, it’s kind of crazy right now because I’m in this—you know—the last four weeks before the book comes out, so it’s a lot of working with PR. But usually it’s writing, it’s working on my blog, it’s—I have contributors who write and submit things and so looking at that stuff, it’s writing new material for stand-up, it’s going to an open mic maybe in the afternoon, maybe one or two open mics in the afternoon. Maybe I’ll have a show at night. And I am meeting a lot more people, I haven’t really found collaborators that I work with regularly yet, but that is something that I want to work on. I’d love to start a podcast like you ladies! That is something I have been thinking about, but I can’t get past coming up with a name! So, I would like to do something like a podcast or more regular content because for me, I’ve realized I love having a schedule and that’s been the hardest thing for me is just to have a consistent schedule.

KL Yeah, I appreciate that. Especially being in a field that is—you know—very much creative, I think people often underestimate how much it helps to have a schedule, how much it helps to have stability, however you can make that happen. So what is great about working as a full time comedian and working the way that you work right now and maybe what’s kind of harder about it?

SC I think what’s great about it is kind of what I was saying before is that I have so many outlets to discover myself and who I really am, which is something that I think is just really important for a life, you know? To know you left everything on the table and you told every story that you wanted to tell and you let everyone know who you are—and you didn’t leave this world without telling everybody that. And I think that’s really important. And then using that to inspire other people and—when I get people writing me that they are starting to draw or are starting to write satire or they are doing something else, that’s really exciting for me, and I hope that I can do more of that, which is create more things to inspire more people to create things. That’s the thing that’s great about it, it’s kind of this journey for me as a person that I get to be on and I don’t have to dedicate the majority of my day to being at a job that I am not that excited about. I can devote most of my day to doing things that get me closer to who I want to be as a person. And the thing that’s hard is staying motivated and, you know, getting out of bed, not getting frustrated to the point where I just feel like I don’t want to do anything because nothing’s working. You know, it’s really hard just when there’s nobody telling you, “hey, there’s a deadline.” You make the deadlines, sometimes you just don’t want to do that thing or you just don’t feel motivated to do that thing and so it’s—I think that’s the hardest thing is finding that consistency and that motivation for me so that I can keep going without having any external people telling me what to do.

[49:00]

SWB Do you have any techniques that you’ve found work for you when you’re having those moments where you’re like, “well what if I just got back under the covers?”

SC Yeah. I have a journal called the “Best Self Journal” and it it has kind of changed my life and if—sometimes I use it and sometimes I don’t. If I don’t use it, it’s very bad. If I use it, it changes my day. And basically what I do is the night before, I will write down every hour of how I’m going to spend the next day and doing that makes me—first of all, it makes me realize, “hey, there are—there are enough hours in the day to get done what you want to do” and also it just is this thing that I keep referring back to throughout the day to kind of stay on track. And so if I have that, it really helps me keep going because I have this plan and I can kind of follow that plan. If there’s nothing, if my day is just an open blue sky, then I will just piss it away on Twitter—and that’s—that’s what I’ll do. So, that has really helped me.

SWB I love the “Best Self Journal.” I know that I’m not going to be my best self necessarily every day, [SC laughs quietly] but thinking about what would I be doing if I was really being my best version of myself in this moment is like—that sounds like a pretty cool exercise.

SC Yeah.

SWB Sarah, this has been really great and we are about out of time, so I have one last question for you, which is just, where can folks follow your work?

SC So, my personal website is sarahcpr.com. s-a-r-a-h-c-p-r.com—c-p-r is just short for Cooper, it doesn’t mean I know CPR or anything like that. And you can see all my events on there and all my press and all that stuff. If you want to check out thecooperreview.com, that has all of the blog posts and hopefully we will return to a regular publishing schedule there as well, once we get out of the book craziness.

SWB Well, that’s awesome. So, everybody, you heard her—follow Sarah and also How to Be Successful Without Hurting Men’s Feelings is going to be on sale by the time you’re listening to this. And even though I’m personally pretty okay with hurting some men’s feelings, I definitely loved it. So, pick it up! And Sarah, thank you so much for being here.

SC Thank you. And the book has mustaches in the back that you can actually wear, so another reason to buy it. [laughs & KL & SWB join in]

KL Perfect. [music fades in, plays for five seconds, and fades out]

[51:20]

Sponsor: Shopify

SWB [Ad spot] Hey, it’s time for a quick career check with Shopify. This week we have Zeina Naboulsi on the line. She’s the executive assistant to Shopify’s CEO, Tobi Lütke, and she’s here to talk about the interview process. Zeina, tell us what you’ve learned!

Zeina Naboulsi Well, one of the pieces of advice we constantly give to candidates is “just be yourself.” And it sounds so clichéd, but it’s true. Three years ago, when I interviewed at Shopify—or even when I recently sat down with Tobi about my new role—I just remember giving myself permission to be authentically me. This alleviated so much pressure. This is a new challenge for me, but going forward, I can look at it from a lens that’s really mine. Interviewing is nerve-wracking enough as it is. Imagine spending the whole time trying to be someone else. Just think, if you can approach an interview being your authentic self, you know that you’re going to show up on day one and every day after that as you.

SWB Thanks, Zeina! That might sound hard to do, but it’s so true. And if you want to work with folks like Zeina, then you should check out Shopify. They’ve got roles in offices around the world, all at shopify.com/careers. [music fades in, plays for five seconds, and fades out]

SWB Probably. Okay, so specifically, tonight me and Katel are going to go and see Courtney Barnett—

KL Ughh!

SWB —and I just love her so much! Her album from earlier this year, “Tell Me How You Really Feel,” has been on repeat for me over and over and over again for the past few months.

KL Me too, I love Courtney Barnett and I remember when she came out with the song “Avant Gardener,” which is essentially a song about her having a full-on public panic attack. And it’s such a great song, I identified with it so much. I really appreciate that she sings about anxiety [laughs] and depression and brings it into her art and she’s just so fucking good, I can not wait.

SWB Yes. You know, there’s just something about her songwriting that really gets me because it’s like it’s quirky and fun, but it’s also often really open about things that are sad or difficult. And so I like that kind of juxtaposition and it feels really honest and kind of disarming, right? Because it feels like—it feels like you’re kind of really getting to know her. And so it makes me happy hearing her voice and it makes me feel like we don’t have to pretend that things are fine when they’re not, but that also, things are going to be okay and it’s okay even if you’re sad.

KL Yeah. Plus I love any opportunity to hang out with you solo, obviously, but we are taking our partners with us tonight, so that’s a bonus. We’re doing a double date! And we’re so cool, we’re doing it on a school night. [laughs][54:01]

SWB I totally still feel like, “oh my god, we’re going out on a school night.” I used to go to a lot of shows in my twenties—all through my twenties I went to shows constantly and I feel like the past few years, I really haven’t made it to as much as I would like. And—you know—part of it is getting older and it gets late and I get tired and I’m not going to lie, that happens and I’m okay with that. I’m actually pretty okay with that. But part of it I think has been because my work life has resulted in a lot of travel—I’m in and out of town, I’m at conferences, it’s sort of like going to a concert can sometimes feel just like a lot. And it’s also just hard to keep up with bands and when they’re going to be in town and am I going to be in town? So, I feel like that’s been less of my life than I’d like it to be, but I’m trying to kind of bring a little bit more balance back around that. So, we saw Sweet Spirit a few months ago. And then just recently me and Will, we went to go and see Liz Phair and relive some awesome nineties vibes, that was also excellent.

KL I’m so sad I missed that.

SWB Yeah, I felt like I was one of the youngs at the show—[KL laughs]

KL Yeah.

SWB —which is also a pretty interesting feeling because I don’t feel like that that often anymore. And so—I don’t know—I like that I feel like I’m kind of coming to terms with where I am in life, which is that I can’t go to everything and I’m also—I’m not going to go out for a drink with you after the show.

SWB But I still fucking love a good, live show and I am so fucking excited to be out there tonight seeing Courtney Barnett. So, fuck yeah to getting out and seeing artists you love!

KL And fuck yeah to badass women musicians.

SWB Fuck yeah! Well, that is it for this week’s episode of No, You Go. NYG is recorded in our home city of Philadelphia and it is produced by Steph Colbourn. Our theme music is by The Diaphone. Thanks to Sarah Cooper for being our guest today.

KL Thanks for listening. And hey, if you like our show, don’t forget to subscribe and rate it wherever you listen to podcasts. Oh, and tell a friend or two. See you again next week!